Oak Bluffs Vacation Rentals

Oak Bluffs is a beautiful peninsula on the north eastern coast of Martha’s Vineyard that is bordered by Nantucket Sound. Renting a vacation home in Oak Bluffs gives you so many options. Our list of vacations rentals include luxury waterfront properties with exceptional views of the sound and quaint Victorian homes that allow you to glimpse deeply into Martha’s Vineyard’s historic past. Vacationing in Oak Bluffs is like taking a trip back in time. Ocean air and private beaches make you feel as though you have Martha’s Vineyard all to yourself.

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Stunning Tri-Level Home, Heated Pool, Screened Porch, Beautifully Landscaped, Walk to Association Tennis Courts

Featured MVVR Listing:

Beautiful Coastal Inspired Retreat features multiple living spaces, a pool, a bluestone patio area, and a deck with an outdoor dining and grill area.  This beautiful home is...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$9,000 - $9,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
$10,000
22
23
24
25
26
27
28
$10,500
29
30
 $15,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$15,000
6
7
8
9
10
11
12
$15,000
13
14
15
16
17
18
19
$15,000
20
21
22
23
24
25
26
$15,000
27
28
29
30
31
 $16,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$16,000
3
4
5
6
7
8
9
$17,500
10
11
12
13
14
15
16
$17,500
17
18
19
20
21
22
23
$17,500
24
25
26
27
28
29
30
$17,000
31
 $11,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$11,000
7
8
9
10
11
12
13
$9,000
14
15
16
17
18
19
20
$9,000
21
22
23
24
25
26
27
$9,000
28
29
30
 
Clean Fee: 
$550 per week
Tax: State & Local: 
11.7

Pool Heated to 80 degrees included in rental rate last Saturday in June to the first Saturday in September. 

 

Pool Heated to 80 degrees, June & September weeks additional $300 propane surcharge per week. 

   

 

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Stunning Luxury Home, Complete Renovation in Main House, Sweet Updated Guest House, Walk to Oak Bluffs Center

Gorgeous Luxury Home, Newly Renovated with Stylish Updates, Walking Distance to Oak Bluffs Center

This stunning bungalow-style home has undergone a complete renovation, blending luxury designer decor with the original...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$6,000 - $9,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
$6,000
22
23
24
25
26
27
28
$7,000
29
30
 $11,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$11,000
6
7
8
9
10
11
12
$9,000
13
14
15
16
17
18
19
$9,000
20
21
22
23
24
25
26
$9,000
27
28
29
30
31
 $15,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$15,000
3
4
5
6
7
8
9
$17,000
10
11
12
13
14
15
16
$17,000
17
18
19
20
21
22
23
$12,000
24
25
26
27
28
29
30
$10,000
31
 $7,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
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$7,000
7
8
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10
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13
$7,000
14
15
16
17
18
19
20
$7,000
21
22
23
24
25
26
27
$7,000
28
29
30
 
Clean Fee: 
$550 per week
Tax: State & Local: 
11.7
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Beautiful Newly Updated Oak Bluffs Home, Nestled on a Large Landscaped Lot in a Quiet Enclave of Homes. 4 Bedrooms. 4.5 Baths

Step inside to discover a welcoming interior, highlighted by a sunroom featuring comfortable seating around the TV. The open first-floor plan seamlessly integrates the main family room complete with a media...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$6,000 - $9,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
$7,000
22
23
24
25
26
27
28
$7,500
29
30
 $8,500
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$8,500
6
7
8
9
10
11
12
$8,500
13
14
15
16
17
18
19
$8,500
20
21
22
23
24
25
26
$9,000
27
28
29
30
31
 $9,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$9,000
3
4
5
6
7
8
9
$12,000
10
11
12
13
14
15
16
$12,000
17
18
19
20
21
22
23
$10,000
24
25
26
27
28
29
30
$10,000
31
 $7,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$7,000
7
8
9
10
11
12
13
$6,000
14
15
16
17
18
19
20
$6,000
21
22
23
24
25
26
27
$6,000
28
29
30
 
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
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Charming , Modern In-Town Oak Bluffs Vacation Home. Walk to Town, Parks, Beach. 4 Bedrooms, Sleeps 8, 3 Baths

This charming Oak Bluffs home is tucked away in a peaceful neighborhood, yet conveniently located just a 10-minute walk to the heart of town, the harbor, and the beach. Meticulously...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$6,500 - $8,500
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 $8,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$8,000
6
7
8
9
10
11
12
$7,000
13
14
15
16
17
18
19
$7,000
20
21
22
23
24
25
26
$7,000
27
28
29
30
31
 $7,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$7,000
3
4
5
6
7
8
9
$7,500
10
11
12
13
14
15
16
$7,500
17
18
19
20
21
22
23
$8,500
24
25
26
27
28
29
30
$6,500
31
 
September 2025
SuMoTuWeThFrSa
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
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Location: 
Oak Bluffs
Sleeps: 
10
Bedrooms: 
5
Baths: 
3
Price Range:
$4,630 - $8,350
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
$5,750
22
23
24
25
26
27
28
$7,000
29
30
 $8,350
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$8,350
6
7
8
9
10
11
12
$9,750
13
14
15
16
17
18
19
$8,350
20
21
22
23
24
25
26
$8,350
27
28
29
30
31
 $11,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$11,000
3
4
5
6
7
8
9
$11,000
10
11
12
13
14
15
16
$11,000
17
18
19
20
21
22
23
$11,000
24
25
26
27
28
29
30
$11,000
31
 $7,750
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$7,750
7
8
9
10
11
12
13
$7,000
14
15
16
17
18
19
20
$6,900
21
22
23
24
25
26
27
$6,800
28
29
30
 $6,700
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7

Rates reduce for available weeks in June & July - see calendar for adjusted rates

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Lovely New 3 Bedroom, 3.5 Bath Home, 15 min walk to Oak Bluffs Center, Inkwell Beach and Town Beach, Sleeps 8, 3 Bedrooms, Plus Loft, 3.5 Baths

Please note: This beautiful new home is in the process of being furnished into April. The photos provided are a sampling of the decor. All furnishings and household items will...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
3
Baths: 
3
Price Range:
$5,230 - $8,010
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
$6,840
22
23
24
25
26
27
28
$6,840
29
30
 $8,010
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$8,010
6
7
8
9
10
11
12
$8,010
13
14
15
16
17
18
19
$8,010
20
21
22
23
24
25
26
$8,010
27
28
29
30
31
 $8,010
August 2025
SuMoTuWeThFrSaWeek
 1
2
$8,010
3
4
5
6
7
8
9
$11,230
10
11
12
13
14
15
16
$11,230
17
18
19
20
21
22
23
$11,230
24
25
26
27
28
29
30
$8,010
31
 $8,010
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$8,010
7
8
9
10
11
12
13
$6,040
14
15
16
17
18
19
20
$6,040
21
22
23
24
25
26
27
$6,040
28
29
30
 $5,230
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7

3 night minimum stay required, May, June, September, October,  4 night minimum July to 7/19

 

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Lovely, Newly Updated Oak Bluffs Home. Multiple Indoor/Outdoor Living/Lounge Areas, Sleeps 8, 10/15 minute Walk to the Vilage Center.

Note: All photos are virtually staged photos by the owner, all new furnishings will be arriving throughout the winter months. 

Welcome to Noble House, a beautifully updated home nestled in a charming neighborhood just...Read more

Location: 
Oak Bluffs
Sleeps: 
9
Bedrooms: 
3
Baths: 
2
Price Range:
$1,650 - $8,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
$6,000
22
23
24
25
26
27
28
$6,000
29
30
 $7,500
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,500
6
7
8
9
10
11
12
$7,500
13
14
15
16
17
18
19
$6,500
20
21
22
23
24
25
26
$8,000
27
28
29
30
31
 $8,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$8,000
3
4
5
6
7
8
9
10
11
12
13
14
15
16
$8,000
17
18
19
20
21
22
23
$8,000
24
25
26
27
28
29
30
$6,200
31
 $6,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,000
7
8
9
10
11
12
13
$6,000
14
15
16
17
18
19
20
$6,000
21
22
23
24
25
26
27
$6,000
28
29
30
 $4,000
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
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Beautiful Oak Bluffs home just blocks from the Center of Town, Ocean Park and Inkwell Beach.

Note: the kitchen is being completely remodeled for summer 2024 and will have all new high-end appliances, Subzero, Thermador, and new cabinets, and counters. 

Summer Joy!  Set in the heart of...Read more

Location: 
Oak Bluffs
Sleeps: 
9
Bedrooms: 
5
Baths: 
2
Price Range:
$5,000 - $7,850
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
$5,500
22
23
24
25
26
27
28
$7,000
29
30
 $7,850
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,850
6
7
8
9
10
11
12
$8,000
13
14
15
16
17
18
19
$8,000
20
21
22
23
24
25
26
$8,000
27
28
29
30
31
 $8,750
August 2025
SuMoTuWeThFrSaWeek
 1
2
$8,750
3
4
5
6
7
8
9
$8,750
10
11
12
13
14
15
16
$10,350
17
18
19
20
21
22
23
$10,350
24
25
26
27
28
29
30
$8,750
31
 $6,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,500
7
8
9
10
11
12
13
$6,500
14
15
16
17
18
19
20
$6,500
21
22
23
24
25
26
27
$6,500
28
29
30
 $5,000
Clean Fee: 
$650 per week
Tax: State & Local: 
11.7

Rates reduced for available weeks in June & July - see calendar for adjusted rates

 

8-minute walk from the ferry dock in Oak Bluffs and 5 minute walk to the Ink Well Beach, and Oak Bluffs Center from the house. 

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Outstanding Designer Home, 15 Min Walk to Oak Bluffs Center, 4 Bedrooms each en suite with TV, Occupancy Limit 9

Stylish Dreamy Home on Dreamer's Way, less than a mile from the town center and beach area! The owners have left nothing out in the way of design and comfort in...Read more

Location: 
Oak Bluffs
Sleeps: 
9
Bedrooms: 
4
Baths: 
4
Price Range:
$7,700 - $7,700
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
$7,200
22
23
24
25
26
27
28
$7,700
29
30
 $8,500
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$8,500
6
7
8
9
10
11
12
$8,500
13
14
15
16
17
18
19
$8,800
20
21
22
23
24
25
26
$9,000
27
28
29
30
31
 $9,200
August 2025
SuMoTuWeThFrSaWeek
 1
2
$9,200
3
4
5
6
7
8
9
$9,700
10
11
12
13
14
15
16
$10,500
17
18
19
20
21
22
23
$11,000
24
25
26
27
28
29
30
$9,500
31
 $8,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$8,000
7
8
9
10
11
12
13
$6,500
14
15
16
17
18
19
20
$5,500
21
22
23
24
25
26
27
$4,500
28
29
30
 
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7

Owner ACCEPTS 3 NIGHT MINIMUM STAYS, MEMORIAL DAY WEEKEND TO JUNE 16TH, AND SEPT 7TH TO THE END OF OCTOBER.

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Beautiful Upscale Contemporary Home, Designer Details Throughout, 4 Bedrooms, 4.5 Baths, Muliple Living Areas

Discover this stunning tri-level vacation home nestled in a peaceful community just on the outskirts of Oak Bluffs and minutes away from Oak Bluffs center, Edgartown Village, downtown Vineyard Haven, and several...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
4
Baths: 
4
Price Range:
$7,500 - $7,500
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
$7,500
29
30
 $7,800
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,800
6
7
8
9
10
11
12
$7,800
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
 $8,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$8,000
3
4
5
6
7
8
9
$8,300
10
11
12
13
14
15
16
$8,300
17
18
19
20
21
22
23
$8,300
24
25
26
27
28
29
30
$7,500
31
 
September 2025
SuMoTuWeThFrSa
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$750 per week
Tax: State & Local: 
11.7
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Stunning New Custom Luxury Home, Oak Bluffs, 18 x 36 Heated Saltwater Pool, Bluestone Patio, 4 Bedrooms 3.5 baths

Tucked just on the outskirts of Oak Bluffs downtown area this spacious architect-designed custom home offers families and friends an outstanding vacation experience. 

Professionally designed by a noted architect this outstanding...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$7,500 - $7,500
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
$8,000
22
23
24
25
26
27
28
$13,500
29
30
 $16,500
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$16,500
6
7
8
9
10
11
12
$15,000
13
14
15
16
17
18
19
$16,500
20
21
22
23
24
25
26
$17,000
27
28
29
30
31
 $18,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$18,000
3
4
5
6
7
8
9
$19,500
10
11
12
13
14
15
16
$20,000
17
18
19
20
21
22
23
$20,000
24
25
26
27
28
29
30
$18,000
31
 $9,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$9,500
7
8
9
10
11
12
13
$7,500
14
15
16
17
18
19
20
$7,500
21
22
23
24
25
26
27
$7,500
28
29
30
 $7,500
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7

Pool Heated to 81 degrees July & August included in Rental Rate

Pool Heated to 81 degrees June & September additional $300 Propane Surcharge

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Charming, 4-bedroom Oak Bluffs Home, pristinely maintained!  The large wraparound porch and backyard patio areas provide the perfect venue for relaxing when not at the beach or out and about...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
4
Baths: 
2
Price Range:
$2,000 - $7,500
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
$2,500
22
23
24
25
26
27
28
$2,500
29
30
 $3,500
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,500
6
7
8
9
10
11
12
$3,000
13
14
15
16
17
18
19
$3,000
20
21
22
23
24
25
26
$3,000
27
28
29
30
31
 $3,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$3,000
3
4
5
6
7
8
9
$5,000
10
11
12
13
14
15
16
$5,750
17
18
19
20
21
22
23
$5,750
24
25
26
27
28
29
30
$5,250
31
 $4,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,000
7
8
9
10
11
12
13
$2,000
14
15
16
17
18
19
20
$2,000
21
22
23
24
25
26
27
$2,000
28
29
30
 $2,000
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7

Parking for two cars only, no on-street parking!

 

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"Endless Summer Vacation" Stylish, Newly Update 3 + Bedroom, Sleeps 8, East Chop Area of Oak Bluffs, Deck Living & Dining Area, Screened Porch,
Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$3,500 - $7,500
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
$4,000
22
23
24
25
26
27
28
$4,000
29
30
 $5,500
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,500
6
7
8
9
10
11
12
$5,000
13
14
15
16
17
18
19
$5,000
20
21
22
23
24
25
26
$5,000
27
28
29
30
31
 $5,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$5,500
3
4
5
6
7
8
9
$7,500
10
11
12
13
14
15
16
$7,500
17
18
19
20
21
22
23
$7,500
24
25
26
27
28
29
30
$5,500
31
 $4,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,500
7
8
9
10
11
12
13
$4,500
14
15
16
17
18
19
20
$4,500
21
22
23
24
25
26
27
$4,500
28
29
30
 $4,500
Clean Fee: 
$330 per week
Tax: State & Local: 
11.7

Owner will rent off weekend dates to accommodate the need for ferry tickets July weeks. 

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Perfect Retreat for Large Families, 1.5 miles to Oak Bluffs Town Center & Beach, Bike Path at end of Street

Spacious and perfect for extended families, featuring multiple attractively furnished living areas, and sleeps 13 comfortably. The lower level of the house features a queen bed, kitchenette, den area with...Read more

Location: 
Oak Bluffs
Sleeps: 
11
Bedrooms: 
5
Baths: 
3
Price Range:
$7,350 - $7,350
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
$7,350
22
23
24
25
26
27
28
$7,350
29
30
 $7,350
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,350
6
7
8
9
10
11
12
$7,350
13
14
15
16
17
18
19
$7,350
20
21
22
23
24
25
26
$7,350
27
28
29
30
31
 $7,350
August 2025
SuMoTuWeThFrSaWeek
 1
2
$7,350
3
4
5
6
7
8
9
$7,350
10
11
12
13
14
15
16
$7,350
17
18
19
20
21
22
23
$7,950
24
25
26
27
28
29
30
$7,950
31
 $7,350
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$7,350
7
8
9
10
11
12
13
$7,350
14
15
16
17
18
19
20
$7,350
21
22
23
24
25
26
27
$7,350
28
29
30
 
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
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East Chop Area, Tri-Level Home with Distant Water views, Located just 1.5 Mi to Oak Bluffs Center

Beautiful summer home with distant water views, located in the desirable East Chop neighborhood.  This 4 bedroom, 3 bath home is located just 1.5 miles from Oak Bluffs Center & Beach. 

The...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$6,500 - $7,150
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
$6,500
22
23
24
25
26
27
28
$6,500
29
30
 $7,150
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,150
6
7
8
9
10
11
12
$7,150
13
14
15
16
17
18
19
$7,150
20
21
22
23
24
25
26
$7,150
27
28
29
30
31
 $7,150
August 2025
SuMoTuWeThFrSaWeek
 1
2
$7,150
3
4
5
6
7
8
9
$7,150
10
11
12
13
14
15
16
$7,150
17
18
19
20
21
22
23
$7,150
24
25
26
27
28
29
30
$7,150
31
 $7,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$7,000
7
8
9
10
11
12
13
$6,500
14
15
16
17
18
19
20
$6,500
21
22
23
24
25
26
27
$6,500
28
29
30
 $6,500
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7

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